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Exploring Historic Boston in 2 Days
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Exploring Historic Boston in 2 Days
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Day 1: Historic Sites & Local Cuisine
Boston, USA
8:00AM
Breakfast at Tatte Bakery & Cafe
Start your day with a delicious breakfast at Tatte Bakery & Cafe known for its freshly baked pastries and artisanal coffee.
Walk 5 minutes from Tatte Bakery to Boston Common.
15, 1 hour
9:30AM
Explore Boston Common
Take a leisurely stroll through the oldest city park in the United States, Boston Common, and enjoy the scenic beauty.
Walk 15 minutes to reach the start of the Freedom Trail.
Free, 1.5 hours
11:00AM
Walk the Freedom Trail
Embark on a historic journey by following the red-brick Freedom Trail that leads you to 16 significant sites of the American Revolution.
Walk 20 minutes to Faneuil Hall Marketplace.
Free, 2 hours
1:00PM
Lunch at Quincy Market in Faneuil Hall Marketplace
Indulge in a variety of local cuisines at Quincy Market within the bustling Faneuil Hall Marketplace.
Walk 10 minutes to the North End neighborhood.
20, 1 hour
2:30PM
Explore the North End
Immerse yourself in the rich Italian heritage of the North End, known for its charming streets, historic sites, and delectable cannoli.
Walk 25 minutes to your accommodation.
Free, 2 hours
4:30PM
Check-in at your hotel or Airbnb
Rest and refresh at your chosen accommodation before heading out for dinner.
Rest and prepare for dinner in the North End.
Varies, N/A
7:00PM
Dinner at Giacomo's Ristorante
Savor authentic Italian dishes at Giacomo's Ristorante, a local favorite known for its delicious seafood and cozy atmosphere.
Walk 10 minutes from your accommodation to Giacomo's Ristorante.
40, 1.5 hours
Find Hotels in Boston
Day 2: Historic Universities & Cultural Districts
Boston, USA
8:30AM
Breakfast at Tatte Bakery & Cafe
Enjoy another delightful breakfast at Tatte Bakery & Cafe to kick off your second day in Boston.
Walk 5 minutes from Tatte Bakery to Harvard University.
15, 1 hour
9:30AM
Explore Harvard University
Discover the prestigious grounds of Harvard University, explore its iconic buildings, and soak in the academic atmosphere.
Take the subway from Harvard Square to Kenmore Station near Fenway Park (25-minute ride).
Free, 2 hours
11:30AM
Visit Fenway Park
Experience the historic Fenway Park, home of the Boston Red Sox, and take a guided tour to learn about its rich baseball history.
Walk 15 minutes to Newbury Street in Back Bay.
25, 1.5 hours
1:30PM
Lunch at Stephanie's On Newbury
Enjoy a delicious lunch at Stephanie's On Newbury, a popular spot on the fashionable Newbury Street offering American cuisine.
Explore the shops and cafes along Newbury Street in Back Bay.
30, 1 hour
2:30PM
Stroll along Newbury Street
Take a leisurely walk down Newbury Street, known for its upscale boutiques, art galleries, and charming brownstones.
Explore nearby landmarks in Back Bay such as Copley Square and the Boston Public Library.
Free, 2 hours
4:30PM
Explore Back Bay
Discover the architectural beauty of Back Bay, including the Victorian brownstones and the picturesque Commonwealth Avenue Mall.
Return to your accommodation for a short rest before dinner.
Free, 1.5 hours
7:00PM
Dinner at Mistral
Indulge in a fine dining experience at Mistral, offering Mediterranean-inspired cuisine in an elegant setting.
Walk or take a short ride to Mistral from your accommodation.
60, 2 hours
Find Hotels in Boston
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Itinerary created by
Plantrip Team
March 31, 2024
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